This article reports on a dyad model of lesson study aimed at scaffolding the theory and practice of learning to teach physical education. Participants were pre-service teachers (PSTs) completing a 38-week Master’s-level Postgraduate Certificate in Education in eastern England, training to teach the secondary age range (11–18 years). A total of 40 PSTs volunteered to participate in the study during their school-based training. A three-year cross-sectional case-study framework involving three distinct cohorts of PSTs allowed for a comparison of data, captured through computer-mediated communication. Dialogue through email communications and electronic evaluations was analysed inductively. Three substantive themes were identified as a result of the PSTs’ experiences: (a) developing confidence in the classroom through collaboration with a peer; (b) developing physical education pedagogies to support students’ individual learning needs; and (c) developing physical education pedagogies to support assessment of students’ progress. The dyad lesson study model provided a safe and non-hierarchical platform for collaboration between PSTs. Peer-to-peer reflection on aspects of their own practice instilled confidence and enhanced understanding, particularly in relation to understanding students’ individual learning needs to promote progress and assessing such progress. Dyad lesson study positively supported PSTs’ professional development against prescribed Teachers’ Standards beyond the formal hierarchical rules and structures associated with the school-based training process. Such collaborative conversations can help to minimise professional isolation for PSTs during their school-based training and address the juxtaposition of connecting the theory of learning to teach with a holistic view of student learning in practice.